(3-Diethoxyphosphoryl-3-fluoroprop-1-ynyl)benzene | 178944-09-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (3-Diethoxyphosphoryl-3-fluoroprop-1-ynyl)benzene
• CAS: 178944-09-7
• 化学式: C₁₃H₁₆FO₃P
• 分子量: 270.24
• InChiKey: KQQUGXJEFSQAJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-Diethoxyphosphoryl-3-fluoroprop-1-ynyl)benzene 在 aluminum oxide 、 Lindlar's catalyst 氢气 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 ((Z)-1-Fluoro-3-phenyl-allyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of α-fluoro-β, γ-alkenylphosphonates and conjugated fluoroenynes from a common intermediate (α-fluoropropargyl) phosphonate

  摘要：

  The efficient preparation of alpha-fluoro-beta,gamma-alkenylphosphonate 3, via catalytic hydrogenation of (alpha-fluoropropargyl)phosphonate ester 1, is described. Conjugated fluoroenynes 4 have been synthesized using a modified Horner Wadsworth Emmons (HWE) olefination of aldehydes or ketones and 1 in relatively good yields. Yields were lowered because of the formation of alpha-fluoro-gamma-hydroxyallenylphosphonate 5 during the reaction. The nature of the counterion was very important in the outcome of the HWE reaction; better yields of fluoroenynes were obtained when a potassium base was used instead of a lithium base. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01017-5
• 作为产物：
  描述：

  3-苯基-2-丙炔-1-醇 在 sodium hydroxide 、 二乙胺基三氟化硫 、 苄基三乙基氯化铵 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.83h， 生成 (3-Diethoxyphosphoryl-3-fluoroprop-1-ynyl)benzene
  参考文献：
  名称：

  Efficient Syntheses of (α-Fluoropropargyl)phosphonate Esters

  摘要：

  DOI：

  10.1021/jo9602027

文献信息

• The preparation of (EtO)2P(O)CFHZnBr and (EtO)2P(O)CFHCu and their utility in the preparation of functionalized α-fluorophosphonates
  作者：Xin Zhang、Weiming Qiu、Donald J. Burton

  DOI：10.1016/s0040-4039(99)00305-6

  日期：1999.4

  The organometallic reagent, (EtO)2P(O)CFHZnBr, was generated in situ in excellent yields via the reaction of (EtO)2P(O)CFHBr with zinc metal. Metathesis with Cu(I)Br gave (EtO)2P(O)CFHCu. The reagents exhibit excellent reactivity with substrates, such as allyl halides, alkynyl halides, vinyl halides, aryl halides and acyl or phosphoryl halides, and provide a useful one flask route to functionalized

  通过（EtO）2 P（O）CFHBr与锌金属的反应，原位生成有机金属试剂（EtO）2 P（O）CFHZnBr 。与Cu（I）Br复分解得到（EtO）2 P（O）CFHCu。该试剂与烯丙基卤，炔基卤，乙烯基卤，芳基卤和酰基或磷酰基卤等底物具有优异的反应性，并为官能化的α-氟代膦酸酯提供了一条有用的烧瓶法。
• Efficient Syntheses of (α-Fluoropropargyl)phosphonate Esters
  作者：Farid Benayoud、Daniel J. deMendonca、Cheryl A. Digits、George A. Moniz、Tanya C. Sanders、Gerald B. Hammond

  DOI：10.1021/jo9602027

  日期：1996.1.1
• Synthesis of α-fluoro-β, γ-alkenylphosphonates and conjugated fluoroenynes from a common intermediate (α-fluoropropargyl) phosphonate
  作者：Farid Benayoud、Ling Chen、George A. Moniz、Antonio J. Zapata、Gerald B. Hammond

  DOI：10.1016/s0040-4020(98)01017-5

  日期：1998.12

  The efficient preparation of alpha-fluoro-beta,gamma-alkenylphosphonate 3, via catalytic hydrogenation of (alpha-fluoropropargyl)phosphonate ester 1, is described. Conjugated fluoroenynes 4 have been synthesized using a modified Horner Wadsworth Emmons (HWE) olefination of aldehydes or ketones and 1 in relatively good yields. Yields were lowered because of the formation of alpha-fluoro-gamma-hydroxyallenylphosphonate 5 during the reaction. The nature of the counterion was very important in the outcome of the HWE reaction; better yields of fluoroenynes were obtained when a potassium base was used instead of a lithium base. (C) 1998 Elsevier Science Ltd. All rights reserved.